Dimethylformamide → methyl (4E)-4-phenyl-4-[[4-[(2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]butanoate

HRID 2299841Notes

Reaction equation

HRID 2299841 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][CH:7]=1.[OH:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)\[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[C:29]1(/[C:22](=[N:21]/[O:20][CH2:19][C:18]2[CH:35]=[CH:36][C:15]([O:14][CH2:2][C:3]3[N:4]=[C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[O:6][CH:7]=3)=[CH:16][CH:17]=2)/[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 35511964-(Chloromethyl)-2-phenyl-1,3-oxazoleHCID 10946929methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoate

Product 1

HCID 10950792methyl (4E)-4-phenyl-4-[[4-[(2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]butanoateYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 4-(chloromethyl)-2-phenyloxazole (250 mg), methyl E-4-(4-hydroxybenzyloxyimino)-4-phenylbutyrate (369 mg), potassium carbonate (325 mg) and N,N-dimethylformamide (7 ml) was stirred at room temperature for 17 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl E-4-phenyl-4-[4-(2-phenyl-4-oxazolylmethoxy)benzyloxyimino]butyrate (320 mg, yield 58%) as a colorless oil from an ethyl acetate-hexane (2:9, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-79d094f70642406ca4a11a4a474b216d
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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